Collect. Czech. Chem. Commun.
1985, 50, 1039-1047
https://doi.org/10.1135/cccc19851039
Partially acetylated sucrose. Preparation of 3-O-acetylsucrose and 3,6'-di-O-acetylsucrose and the analysis of mixtures of O-acetyl derivatives of sucrose of various degrees of acetylation by thin-layer chromatography with flame-ionization detection
Karel Čapeka, Tomáš Vydraa, Jindra Čapkováa, Mojmír Rannýb, Markéta Bláhováb and Petr Sedmerac
a Laboratory of Monosaccharides, Prague Institute of Chemical Technology, 166 28 Prague 6
b Research Institute of Fat Industry (detached laboratory), Prague Institute of Chemical Technology, 166 28 Prague 6
c Microbiological Institute, Czechoslovak Academy of Sciences, Prague
Abstract
Partial deacetylation of 3,3',4',6'-tetra-O-acetyl-l',2 : 4,6-di-O-isopropylidene sucrose (V) with aluminum oxide impregnated with potassium carbonate gave a mixture of 3,6'-di-O-acetyl-l',2 : 4,6-di-O-isopropylidenesucrose (VI) and 3-O-acetyl-l',2 : 4,6-di-O-isopropylidenesucrose (VII). 3,6'-di-O-acetylsucrose (IX) and 3-O-acetylsucrose (X) were prepared on deacetalation of compounds VI and VII, respectively. The structure of compounds IX and X was proved by 13C NMR and mass spectra of their deuterioacetyl derivatives XI and XII. Using procedures described in literature 3,3',4',6'-tetra-O-acetylsucrose (IV), 2,3,3',4',6-penta-O-acetylsucrose (III), l',2,3,3',4',6'-hexa-O-acetylsucrose (II) and 1',2,3,3',4,4',6-hepta-O-acetylsucrose (I) were prepared. These acetyl derivatives, sucrose and their octa-O-acetyl derivative were analysed by thin-layer chromatography with flame-ionization detection either separately or in mixtures. A chromatogram of the mixture was identical with a chromatogram of a mixture of O-acetyl derivatives of sucrose formed on deacetylation of octa-O-acetylsucrose with aluminum oxide impregnated with potassium carbonate; from this it follows that under the conditions of analysis O-acetyl derivatives of sucrose are separated on the basis of the degree of acetylation.
